While some prefer the barbecues, beers and skin-baring of summer, and others favour the shorter days and longer nights of winter, there’s no season that captures my heart and spirit quite like fall. With its promise of new chapters and new loves, it oozes optimism and growth. It even smells good, like cinnamon and firewood.
So each year, I make the most of the fleeting season by diving into films that emulate those very feelings, not to mention my mood board — movies filled with thick cable-knit sweaters, swirling leaves and massive feasts.
If that sounds just right to you, here are some flicks to cue up over the coming weeks — including some that are as moody and mystical as the darker vibes that autumn ushers in, too.
Golden-hour romance
Days of Heaven (1978)
Terrence Malick’s pastoral masterpiece isn’t a conventional romance, but its love triangle set against the wheat fields of Texas (in reality, the wheat fields of Alberta) is both sweeping and intimate. The cinematography — capturing harvests, crisp skies and heavy winds — imbues the film with an autumnal melancholy. Meanwhile, the story’s tender, tragic entanglements echo fall’s mix of beauty and impermanence, and might have you craving your own slow-burn affair.
The Cider House Rules (1999)
Set in rural New England, this coming-of-age romance follows Homer Wells (Tobey Maguire), a young man raised in a Maine orphanage, as he strikes out on his own and falls for Candy Kendall (Charlize Theron). The moody apple orchards and vibrant leaves make this nostalgic film perfect for curling up with on a long, chilly night. (To dive even deeper into the tale, read American Canadian author John Irving’s sumptuous source novel — by a fire, if you can!)
When Harry Met Sally… (1989)
Few movies capture the crisp and sexy vibe of autumn on the East Coast quite like this classic, penned by rom-com savant Nora Ephron. It’s centred on the perennial question: can men and women really be friends? (If you know rom-coms, you know the answer.) Expect tons of witty banter between Harry (Billy Crystal) and Sally (Meg Ryan) against a backdrop of golden Central Park leaves and cable-knits the film has become iconic for. A comfort watch if there ever was one.
A hint of Halloween
Practical Magic (1998)
This delicious cult favourite serves up the perfect combo of witchcraft and sisterhood. It features the magical pairing of Sandra Bullock and Nicole Kidman as Sally and Gillian Owens, sisters who struggle to cope with their very messy romantic lives, family curses and a narrow-minded small town. Watch it for its crispy New England setting; perfectly oversized sweaters and crushed-velvet dresses; and a candlelit kitchen that would make Nancy Meyers proud.
Kiki’s Delivery Service (1989)
Hayao Miyazaki’s animated gem follows young witch Kiki as she leaves home with her talking cat, Jiji (voiced by Canadian comedian Phil Hartman in the English dub), and learns to make her way in a breezy seaside town. While it’s not a Halloween film in the traditional sense, focusing more on themes of independence and self-discovery, it does feature many broomstick flights and a little gentle magic. The warm visuals also make it ideal for a fall evening with the family.
The Witches of Eastwick (1987)
A mischievous dark comedy, this film sees three women (played by the fabulous trio that is Cher, Susan Sarandon and Michelle Pfeiffer) discover their powers — and desires — when a charming and devilish stranger (Jack Nicholson) arrives in town. With its stormy East Coast backdrop and endless satirical bite, it captures both the playful and sinister spirit of the season. Its campy glamour and big, poofy wigs make it perfectly wicked for a friends’ night in, too.
Campus core
Good Will Hunting (1997)
Set against the ivy-clad brick of MIT and Harvard, this unforgettable drama follows janitor and math prodigy Will Hunting (Matt Damon) as he’s pushed to confront his past and embrace his potential with the help of a compassionate therapist (Robin Williams in perhaps his most moving role). The campus scenes, many which were shot at the University of Toronto, pair perfectly with the movie’s themes of self-discovery and change, and suit autumn’s reflective mood to a tee. And for even more Robin Williams and fall feels, queue up Dead Poets Society (1989) — an ideal double feature.
Rushmore (1998)
Few directors have cornered the fall season as well as Wes Anderson, and his offbeat dramedy Rushmore is steeped in collegiate eccentricity. In the film, prep-schooler Max Fischer (Jason Schwartzman) throws himself into plays, clubs and many a scheme and shenanigan as he pursues an unlikely romance with a teacher, all while sparring with a wealthy industrialist (Bill Murray). It’s quirky, it’s tart and, fair warning, might even spur a school-supply shopping spree.
Mona Lisa Smile (2003)
At 1950s Wellesley College, art history professor Katherine Watson (Julia Roberts) challenges her female students (Kirsten Dunst, Maggie Gyllenhaal, Julia Stiles and more) to envision futures beyond marriage. The film’s lecture halls create a nostalgic setting, while its exploration of shifting gender roles offers space for discussion after the credits roll. Plus, its parade of long plaid skirts, tailored blazers and scarlet lips is sure to appeal to lovers of preppy fall fashion.
Moody melodrama
The Iron Giant (1999)
Though it’s an animated film about a boy and his robot, Brad Bird’s The Iron Giant brims with autumnal melancholy. (In fact, no film has ever made this writer sob so ugly.) Set in a — you guessed it — small New England town during the Cold War, it follows a boy named Hogarth who discovers and quickly befriends a massive robot from space. Its muted palette of greys and browns, alongside themes of sacrifice and friendship, are sure to give you real-life chills.
Once Upon a Time in Anatolia (2011)
Nuri Bilge Ceylan’s hypnotic police procedural follows investigators searching for a buried body across the Anatolian steppes. Long night sequences and quiet roadside conversations lend the Turkish-language film an eerie, chilly quality that’s perfect for autumn evenings. At the same time, its slow unraveling of secrets mirrors the introspection that often comes with fall, making it an ideal pick for those looking to settle into something more contemplative.
Petite Maman (2021)
This delicate drama from French director and screenwriter Céline Sciamma centres on a young girl grieving her grandmother’s death who meets a mysterious child her own age in the woods. While what unfolds is anything but expected, the film’s setting of misty forests and swirling air capture a very familiar autumn atmosphere. And with its tender exploration of memory, time and maternal bonds, it offers a soft, if bittersweet, comfort as well.
Ordinary People (1980)
Robert Redford’s directorial debut, starring legendary Canadian actor Donald Sutherland, examines a family fractured by grief after the accidental death of a son. Suburban Chicago, pale skies and brittle leaves you can practically feel crunching under your feet give the film an austere texture that mirrors its emotional landscape. Its exploration of repression, guilt and reconciliation make it a definitive moody melodrama — quiet and sombre, like the season itself.
